6 Startup Lessons I Found When I Began Jet Skiing to Work…

A few years back, I grew frustrated with my commute from Seattle to Bellevue and took matters into my own hands. I bought a used jet ski and began journeying to work over Lake Washington, cutting my travel time in half.

The scenery is breathtaking, especially when Mt. Rainier breaks through the cloud in the distance. But, there are hazards on the water, especially if you venture out on the Puget Sound, and some of these provide valuable lessons for business, and for life more broadly.

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Reflecting on when my company, Smartsheet, was just getting off the ground, I started thinking about how these lessons could be helpful to new business leaders. I came up with some advice that I hope will be useful to those who are just starting this exciting stage of their career.

Start at full throttle from the dock.

If you’re heading into choppy waters, decide a course of action and stick to it. If you’re not hard on the throttle and the wind picks up when you leave shore, you’re likely to find yourself dumped back on the dock. Like many things in life, decisiveness is key.

Twelve years ago, I made the decision to leave Onyx Software and join Smartsheet, a startup at the time. This was a huge decision — my daughters were 2 and 5 and I was taking a 60 percent cut in salary to make the move. My wife and I weighed the risks carefully, planning to go through a lean 18 months while Smartsheet was getting off the ground.

I stuck with it, and of course I’m glad I did. But, before you embark on a venture, know what you’re getting into. Evaluate the risks — and once you’ve made the call, be committed to it.

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Read the charts.

It’s important to know what the currents are doing. If you’re pitching a group of investors, be sure you know what’s happening in your market that week, because they want to know you understand the context you’re operating in.

If the markets are against you, that doesn’t necessarily mean you stay home. If you’re seeing amazing pick-up with customers and can show you’ve been successful during a tough period, that might be the exact time to ask for the money. Sometimes it’s fine to battle the tides — just know if you’re in a kayak or a speedboat with two engines behind you.

Learn from the showboaters. 

When the Costa Concordia ran aground in dramatic fashion off the Tuscan coast a few years ago, the cruise line admitted the captain had been showboating — sailing too close to shore in order to impress those on land or on deck.

In business, a lot of people ask me about the things that go right: “Tell me about your conversion rate.” “How do you optimize your website?” But, curiosity around what went wrong is just as important. What can you learn from that person who hired an overpaid sales exec who flamed out?

Tech firms in the Seattle area are generous about sharing advice — because they know how hard it is to mimic success. Pay attention to the tough lessons others learn the hard way. It’s a great way not to end up on the rocks.

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Keep calm and motor on.

If I’m in the middle of the bay and the water gets choppy, I remember a phrase I once heard from the passenger next to me on a turbulent flight: “It’s not a safety issue, it’s a comfort issue.” Some things in life are going to make you feel damned uncomfortable, but keep your wits about you and there’s a chance you’ll make it through unscathed.

A couple of years ago, we pushed out a new version of our service based on a brand-new software architecture. We’d prepared well and everything went smoothly — until it didn’t. We could have panicked and rolled back to the previous version, but that would have been a black eye for us and a huge disappointment for our customers. We worked through the night, hammered out the bugs and our customers thanked us for it.

Don’t abandon ship every time a big wave comes along. Most situations aren’t life threatening, and if you stay present, persistent and professional, you’ll make it through the rough water.

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One engine is good, two engines are better.

If you leave the lake and head for the salt water, you can’t be too prepared. Don’t be that person who loses an engine and needs to be rescued by the Coast Guard. There’s no such thing as too much redundancy at sea.

Building a resilient, reliable platform is easier when you’re a startup. It’s much harder and more disruptive to redesign your architecture and add that redundancy later on, when you have thousands of paying customers. If you believe you’re going to succeed, design it properly from the beginning.

Redundancy applies to personnel, too. If there’s only one person in your company who knows how your product was architected, you’re asking for trouble.

Obey the rules.

I was out cruising with my daughter once when the Coast Guard boarded us for a routine safety check. It turned out one of my flares had expired two months prior and I ended up with a $1,500 citation. It pays to follow the rules.

For a startup, that doesn’t only mean written rules for things like taxes and contracts. The unwritten rules are just as important. Don’t make commitments you can’t keep. Don’t oversell your product. Don’t hire someone without telling them what they’re getting into. In life and in business, things can come back around to bite you.

Being on a lake or the ocean is an exciting place to be, but much like running a startup, you need to keep your wits about you, an eye on the conditions and be prepared to adjust course when the circumstances demand it. I’ve had a great voyage on this ship we call Smartsheet, and I’m proud of the talented crew who have navigated our course. I hope your voyage will be as successful.